α-Glucosidase Inhibition by Usnic Acid Derivatives.
Dakin oxidation
benzylidene derivative
usnic acid
α-glucosidase inhibition
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Apr 2021
Apr 2021
Historique:
received:
04
11
2020
accepted:
04
02
2021
pubmed:
5
2
2021
medline:
27
7
2021
entrez:
4
2
2021
Statut:
ppublish
Résumé
This study investigated a set of new potential antidiabetes agents. Derivatives of usnic acid were designed and synthesized. These analogs and nineteen benzylidene analogs from a previous study were evaluated for enzyme inhibition of α-glucosidase. Analogs synthesized using the Dakin oxidative method displayed stronger activity than the pristine usnic acid (IC
Identifiants
pubmed: 33538053
doi: 10.1002/cbdv.202000906
doi:
Substances chimiques
Benzofurans
0
Glycoside Hydrolase Inhibitors
0
usnic acid
0W584PFJ77
alpha-Glucosidases
EC 3.2.1.20
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000906Informations de copyright
© 2021 Wiley-VHCA AG, Zurich, Switzerland.
Références
J. S. Johansen, A. K. Harris, D. J. Rychly, A. Ergul, ‘Oxidative stress and the use of antioxidants in diabetes: linking basic science to clinical practice’, Cardiovasc. Dis. 2005, 4-5.
I. Tzoulaki, M. Molokhia, V. Curcin, M. P. Little, C. J. Millett, A. Ng, R. I. Hughes, K. Khunti, M. R. Wilkins, A. Majeed, ‘Risk of cardiovascular disease and all-cause mortality among patients with type 2 diabetes prescribed oral antidiabetes drugs: retrospective cohort study using UK general practice research database’, Br. Med. J. 2009, 339-347.
E. M. Lonn, S. Yusuf, V. Dzavik, C. I. Doris, Q. Yi, S. Smith, A. Moore-Cox, J. Bosch, W. A. Riley, K. K. Teo, ‘Effects of ramipril and vitamin E on atherosclerosis: the study to evaluate carotid ultrasound changes in patients treated with ramipril and vitamin E (SECURE)’, Circulation 2001, 103, 919-925.
K. Müller, ‘Pharmaceutically relevant metabolites from lichens’, Appl. Microbiol. Biotechnol. 2001, 56, 9-16.
İ. Gulçin, P. Taslimi, A. Aygün, N. Sadeghian, E. Bastem, O. I. Kufrevioglu, F. Turkan, F. Şen, ‘Antidiabetic and antiparasitic potentials: Inhibition effects of some natural antioxidant compounds on α-glycosidase, α-amylase and human glutathione S-transferase enzymes’, Int. J. Biol. Macromol. 2018, 119, 741-746.
J. Boustie, S. Tomasi, M. Grube, ‘Bioactive lichen metabolites: alpine habitats as an untapped source’, Phytochem. Rev. 2011, 10, 287-307.
K. Ingolfsdottir, ‘Usnic acid’, Phytochemistry 2002, 61, 729-736.
E. Erba, D. Pocar, L. M. Rossi, ‘New esters of R-(+)-usnic acid’, Il Farmaco 1998, 53, 718-720.
M. Takai, Y. Uehara, J. A. Beisler, ‘Usnic acid derivatives as potential antineoplastic agents’, J. Med. Chem. 1979, 22, 1380-1384.
M.-A. Bazin, A.-C. Le Lamer, J.-G. Delcros, I. Rouaud, P. Uriac, J. Boustie, J.-C. Corbel, S. Tomasi, ‘Synthesis and cytotoxic activities of usnic acid derivatives’, Bioorg. Med. Chem. 2008, 16, 6860-6866.
D. N. Sokolov, V. V. Zarubaev, A. A. Shtro, M. P. Polovinka, O. A. Luzina, N. I. Komarova, N. F. Salakhutdinov, O. I. Kiselev, ‘Anti-viral activity of (−)- and (+)-usnic acids and their derivatives against influenza virus A (H1 N1) 2009’, Bioorg. Med. Chem. Lett. 2012, 22, 7060-7064.
A. A. Shtro, V. V. Zarubaev, O. A. Luzina, D. N. Sokolov, O. I. Kiselev, N. F. Salakhutdinov, ‘Novel derivatives of usnic acid effectively inhibiting reproduction of influenza A virus’, Bioorg. Med. Chem. 2014, 22, 6826-6836.
N. R. Vanga, A. Kota, R. Sistla, M. Uppuluri, ‘Synthesis and anti-inflammatory activity of novel triazole hybrids of (+)-usnic acid, the major dibenzofuran metabolite of the lichen Usnea longissima’, Mol. Diversity 2017, 21, 273-282.
H. Y. Ebrahim, M. R. Akl, H. E. Elsayed, R. A. Hill, K. A. El Sayed, ‘Usnic acid benzylidene analogs as potent mechanistic target of rapamycin inhibitors for the control of breast malignancies’, J. Nat. Prod. 2017, 80, 932-952.
V.-K. Nguyen, J. Sichaem, H.-H. Nguyen, X. H. Nguyen, T.-T.-L. Huynh, T.-P. Nguyen, N. Niamnont, D.-H. Mac, D.-D. Pham, W. Chavasiri, K.-P.-P. Nguyen, T.-H. Duong, ‘Synthesis and cytotoxic evaluation of usnic acid benzylidene derivatives as potential anticancer agents’, Nat. Prod. Res. 2019, 1-10.
K. Van Nguyen, T.-H. Duong, K. P. P. Nguyen, E. Sangvichien, P. Wonganan, W. Chavasiri, ‘Chemical constituents of the lichen Usnea baileyi (Stirt.) Zahlbr’, Tetrahedron Lett. 2018, 59, 1348-1351.
J. P. Kutney, J. D. Leman, P. J. Salisbury, T. Yee, I. H. Sánchez, ‘Studies in the usnic acid series. IX. The biodegradation of (+)-usnic acid by Mucor globosus’, Can. J. Chem. 1984, 62, 320-325.
K. Takahashi, M. Takani, ‘Usnic Acid. XIV. The Photo-Oxidation of Usnic Acid’, Chem. Pharm. Bull. 1978, 26, 3585-3587.
F. Nan, J. Li, Y. Chen, Y. Zhang, M. Gu, H. Zhang, ‘Isoquinoline-1,3,4-trione compounds, the synthetic method and the use thereof’, US Patents, No. 7,683,073, 2010.
Y.-H. Chen, Y.-H. Zhang, H.-J. Zhang, D.-Z. Liu, M. Gu, J.-Y. Li, F. Wu, X.-Z. Zhu, J. Li, F.-J. Nan, ‘Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors’, J. Med. Chem. 2006, 49, 1613-1623.
K. Alder, R. Reubke, ‘Über vic.-Triketone der Bicyclo-[1.2.3]-octan- und der Bicyclo-[2.2.3]-nonan-Reihe’, Chem. Ber. 1958, 91, 1525-1535.
T. Utsukihara, M. Sato, M. Kawamoto, K.-i. Itoh, H. Sakamaki, M. Kuniyoshi, C. A. Horiuchi, ‘Biotransformation of aromatic heterocyclic compounds by Caragana chamlagu and Wasabia japonica’, J. Mol. Catal. B 2007, 48, 59-63.
M. Takemoto, Y. Iwakiri, Y. Suzuki, K. Tanaka, ‘A mild procedure for the oxidative cleavage of substituted indoles catalyzed by plant cell cultures’, Tetrahedron Lett. 2004, 45, 8061-8064.
O. Trott, A. J. Olson, ‘AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading’, J. Comput. Chem. 2010, 31, 455-461.
N. T. Nguyen, T. H. Nguyen, T. N. H. Pham, N. T. Huy, M. V. Bay, M. Q. Pham, P. C. Nam, V. V. Vu, S. T. Ngo, ‘Autodock Vina Adopts More Accurate Binding Poses but Autodock4 Forms Better Binding Affinity’, J. Chem. Inf. Model. 2020, 60, 204-211.
A. Bhatia, B. Singh, R. Arora, S. Arora, ‘In Vitro evaluation of the α-glucosidase inhibitory potential of methanolic extracts of traditionally used antidiabetic plants’, BMC Complementary Altern. Med. 2019, 19, 74-82.
Y. Kurakata, A. Uechi, H. Yoshida, S. Kamitori, Y. Sakano, A. Nishikawa, T. Tonozuka, ‘Structural insights into the substrate specificity and function of Escherichia coli K12 YgjK, a glucosidase belonging to the glycoside hydrolase family 63’, J. Mol. Biol. 2008, 381, 116-128.
A. Faridmoayer, C. H. Scaman, ‘Truncations and functional carboxylic acid residues of yeast processing α-glucosidase I’, Glycoconjugate J. 2007, 24, 429-437.
M. K. Barker, D. R. Rose, ‘Specificity of processing α-glucosidase I is guided by the substrate conformation crystallographic and in silico studies’, J. Biol. Chem. 2013, 288, 13563-13574.
T. M. Gloster, J. P. Turkenburg, J. R. Potts, B. Henrissat, G. J. Davies, ‘Divergence of catalytic mechanism within a glycosidase family provides insight into evolution of carbohydrate metabolism by human gut flora’, Chem. Biol. 2008, 15, 1058-1067.
T. H. Nguyen, B. H. Um, S. M. Kim, ‘Two Unsaturated Fatty Acids with Potent α-Glucosidase Inhibitory Activity Purified from the Body Wall of Sea Cucumber (Stichopus japonicus)’, J. Food Sci. 2011, 76, 208-214.
J. Gasteiger, M. Marsili, ‘Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges’, Tetrahedron 1980, 36, 3219-3228.
G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, ‘AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility’, J. Comput. Chem. 2009, 30, 2785-2791.
J. Liu, X. Wang, S. Geng, B. Liu, G. Liang, ‘Inhibitory mechanism of taxifolin against α-glucosidase based on spectrofluorimetry and molecular docking’, Nat. Prod. Commun. 2017, 12, 1725-1728.